AI Vendor Evaluations & Management Associate Director

Sidley Austin LLP (IL LLP); Chicago (IL); Hybrid; USD 200,000 - 264,000; Full time

Job summary

Sidley Austin LLP in Chicago seeks an AI Vendor Evaluations & Management Associate Director to lead evaluation, selection, and ongoing governance of AI tools for the firm's legal and business needs. You will collaborate across IT, Information Security, Risk, General Counsel, and Procurement to deploy AI solutions, stay current with market trends, and mentor a team while managing vendor relationships.

The role emphasizes evidence-based recommendations, licensing governance, and scalable processes

Qualifications

• Bachelor’s degree in liberal arts, technology, or related field (or equivalent work experience).
• Minimum 8 years of experience in product management, technology evaluation, vendor management, or a similar role.
• Proven experience evaluating, piloting, or procuring AI or enterprise software tools with rigorous assessments.
• Experience managing enterprise software platforms, including user management and license governance.
• Broad knowledge of AI tools for legal work and ability to stay current with evolving market.
• Proven ability to lead, mentor, and develop a team in a fast-moving environment.
• Experience managing executive-level vendor relationships, negotiations, and escalations.
• Excellent communication and facilitation skills bridging vendors, IT, and leadership.

Responsibilities

• Lead evaluation and selection of legal and general-purpose AI tools with frameworks and scoring.
• Oversee relationships with AI and technology vendors, including performance and contracts.
• Roll out and manage general-purpose AI platforms with governance, licensing, and usage monitoring.
• Develop recommendations on AI products based on requirements, user feedback, and market trends.
• Coordinate vendor procurement, security review, data protection, and deployment with stakeholders.
• Monitor developments in the legal AI market and provide insights to leadership.
• Establish processes and standards for AI tool evaluation, governance, and performance assessment.
• Collaborate with practice groups to translate business needs into criteria for vendors and tools.
• Manage, coach, and develop team members and set performance expectations.
• Provide leadership on vendor and platform issues to support adoption of Firm-approved AI tools.

Skills

Vendor management

AI evaluation

Leadership

Stakeholder communication

Cross-functional

Education

Bachelor's degree

Experience in tech evaluation

Job description

The AI Vendor Evaluations & Management Associate Director leads the evaluation, selection, and ongoing management of AI tools and platforms supporting the Firm's legal and business needs. The role develops structured approaches for assessing AI products, provides recommendations regarding technology investments, oversees relationships with AI vendors, and leads the operational management and governance of general-purpose AI platforms in partnership with IT and other Firm stakeholders. Serving as a subject matter expert on the evolving legal AI market, the Associate Director works across practice groups, IT, Information Security, Risk, General Counsel, and Procurement to support informed technology decisions, effective deployment, and sustainable use of AI solutions across the Firm.

Duties and Responsibilities:

• Lead the evaluation and selection process for legal and general-purpose AI tools, developing evaluation frameworks, scoring criteria, and methodologies that support clear, evidence-based recommendations.
• Oversee relationships with AI and technology vendors, including performance, escalations, product roadmaps, service commitments, and coordination of contractual obligations.
• Lead the rollout and ongoing operational management of general-purpose AI platforms in partnership with IT, including governance, licensing, access, usage monitoring, platform configuration, and support processes.
• Develop recommendations regarding AI products and platforms based on Firm requirements, product capabilities, user feedback, market developments, risk considerations, and total value.
• Partner with Procurement, Information Security, Risk, General Counsel, IT, and other stakeholders to coordinate vendor procurement, security assessment, data protection, compliance review, and deployment requirements.
• Monitor and assess developments in the legal AI market, including emerging products, capabilities, pricing models, and market trends, and provide relevant insights and recommendations to Firm and practice leadership.
• Establish and improve processes, standards, documentation, and operating practices for AI tool evaluation, vendor management, platform governance, and ongoing performance assessment.
• Collaborate with practice groups and business functions to identify requirements, translate business needs into technology and vendor criteria, and communicate technical and operational considerations to stakeholders.
• Manage, coach, and develop team members, establish priorities and performance expectations, and build team capabilities as the Firm's AI program evolves.
• Provide leadership on complex vendor and platform issues, coordinating appropriate resources and stakeholders to resolve escalations and support effective adoption and use of Firm-approved AI tools.

Education and/or Experience:

Required:

• Bachelor’s degree in a liberal arts, technology, or related field; or equivalent work experience.
• A minimum of 8 years of experience in product management, technology evaluation, vendor management, or a similar role.
• Demonstrated experience evaluating, piloting, or procuring AI or enterprise software tools; able to design and run rigorous competitive assessments and translate findings into actionable recommendations for senior stakeholders.
• Experience managing and administering enterprise software platforms, including user management, license governance, usage reporting, and vendor support coordination.
• Broad familiarity with the current landscape of AI tools relevant to legal work including general-purpose platforms and legal-specific products, with the curiosity and discipline to stay current as the market evolves rapidly.
• Proven ability to lead, mentor, and develop a team; experience managing direct reports in a fast-moving, cross-functional environment.
• Demonstrated success managing external vendor relationships, including negotiations, escalations, and joint delivery.
• Excellent communication and facilitation skills; able to bridge vendors, IT, and non-technical senior stakeholders including partners and firm leadership, and to build consensus around technology decisions.

Preferred:

• Experience in a regulated professional-services environment such as a law firm, financial services, healthcare, or consulting organization.
• Hands-on experience with a broad range of legal AI tools across research, drafting, contract analysis, e-discovery, and tax/regulatory categories; familiarity with document management systems is a plus.
• Experience with enterprise identity, data governance, and security review processes.

Other Skills and Abilities:

• Strong organizational skills
• Strong attention to detail
• Good judgment
• Strong interpersonal communication skills
• Strong analytical and problem-solving skills
• Able to work harmoniously and effectively with others
• Able to preserve confidentiality and exercise discretion
• Able to work under pressure
• Able to manage multiple projects with competing deadlines and priorities

#LI-OE1 #LI-Hybrid

Applicants must be authorized to work in the United States without the need for employer sponsorship, now or in the future.

The target salary range for this role is: $200,000 - $264,000 if located in Illinois. Salaries vary by location and are based on numerous factors, including, but not limited to, the relevant market, skills, experience, and education of the selected candidate. Our compensation package also includes bonus eligibility and a comprehensive benefits program. Benefits information can be found at Sidley.com/Benefits.

To perform this job successfully, an individual must be able to perform the Duties and Responsibilities above satisfactorily and meet the requirements. The requirements listed above are representative of the minimum knowledge, skill, and/or ability required. Reasonable accommodations will be made to enable individuals with disabilities to perform the essential functions of the job.

Sidley Austin LLP is an Equal Opportunity Employer.

Sidley is an elite global law firm with a known reputation of deploying innovative strategies to achieve powerful results. Business professionals are essential to the firm’s ability to deliver the highest quality legal services to our clients. We are always looking for talented, motivated individuals who thrive in a performance-driven culture to join our team. We encourage you to explore current openings and check back for future opportunities that align with your skills, experience, and career goals.

Sidley employs approximately 2,300 lawyers working with our clients in complex transactional, restructuring, crisis management, investigation, regulatory, and litigation matters. Our 160 years of perspective and reach are truly global, supported by 21 offices strategically situated in key commercial, regulatory, and financial centers across the world. Our lawyers and business professionals, fluent in more than 75 languages, possess the cultural awareness and cross-border legal acumen needed to bring clarity to a dynamic business landscape.